RU2337753C1 - Модифицированная ионообменная смола и способ получения бисфенолов - Google Patents
Модифицированная ионообменная смола и способ получения бисфенолов Download PDFInfo
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- RU2337753C1 RU2337753C1 RU2007104029A RU2007104029A RU2337753C1 RU 2337753 C1 RU2337753 C1 RU 2337753C1 RU 2007104029 A RU2007104029 A RU 2007104029A RU 2007104029 A RU2007104029 A RU 2007104029A RU 2337753 C1 RU2337753 C1 RU 2337753C1
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- Prior art keywords
- carbon atoms
- exchange resin
- compound
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- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical class C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 title claims abstract description 77
- 238000000034 method Methods 0.000 title claims abstract description 40
- 229930185605 Bisphenol Natural products 0.000 title claims abstract description 19
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 110
- 238000006243 chemical reaction Methods 0.000 claims abstract description 94
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 88
- 239000003054 catalyst Substances 0.000 claims abstract description 85
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
- 239000003456 ion exchange resin Substances 0.000 claims abstract description 45
- 229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 45
- 125000003118 aryl group Chemical group 0.000 claims abstract description 38
- 239000002253 acid Substances 0.000 claims abstract description 36
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 27
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 25
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 22
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 19
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 19
- 239000012634 fragment Substances 0.000 claims abstract description 17
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 17
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 38
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 24
- 230000002378 acidificating effect Effects 0.000 claims description 21
- -1 haloalkyl phosphonium Chemical compound 0.000 claims description 20
- 229910052698 phosphorus Inorganic materials 0.000 claims description 17
- 125000004437 phosphorous atom Chemical group 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 150000001768 cations Chemical class 0.000 claims description 12
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 6
- 150000002576 ketones Chemical class 0.000 claims description 5
- 150000002989 phenols Chemical class 0.000 claims description 5
- 229920001577 copolymer Polymers 0.000 claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims 2
- 125000000524 functional group Chemical group 0.000 claims 1
- 150000004714 phosphonium salts Chemical class 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 abstract description 66
- 239000000126 substance Substances 0.000 abstract description 43
- 239000011347 resin Substances 0.000 abstract description 18
- 229920005989 resin Polymers 0.000 abstract description 18
- 230000000694 effects Effects 0.000 abstract description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 2
- 239000000047 product Substances 0.000 description 62
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 57
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 54
- 239000000243 solution Substances 0.000 description 52
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 40
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 38
- 239000000203 mixture Substances 0.000 description 34
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- 239000007787 solid Substances 0.000 description 33
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- 238000003786 synthesis reaction Methods 0.000 description 23
- 239000007864 aqueous solution Substances 0.000 description 22
- 239000003729 cation exchange resin Substances 0.000 description 21
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 19
- 125000000753 cycloalkyl group Chemical group 0.000 description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 19
- 239000012071 phase Substances 0.000 description 19
- 125000003396 thiol group Chemical group [H]S* 0.000 description 17
- 238000003756 stirring Methods 0.000 description 16
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 13
- 229910001873 dinitrogen Inorganic materials 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 12
- 238000004811 liquid chromatography Methods 0.000 description 12
- 239000002245 particle Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 9
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 229910052710 silicon Inorganic materials 0.000 description 9
- 125000004450 alkenylene group Chemical group 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 6
- 230000007423 decrease Effects 0.000 description 6
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 238000005342 ion exchange Methods 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 125000000542 sulfonic acid group Chemical group 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 150000001767 cationic compounds Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000004445 quantitative analysis Methods 0.000 description 3
- 239000011973 solid acid Substances 0.000 description 3
- 230000008961 swelling Effects 0.000 description 3
- QQQZOCKWAKGIBQ-UHFFFAOYSA-N triphenyl(3-sulfanylpropyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCS)C1=CC=CC=C1 QQQZOCKWAKGIBQ-UHFFFAOYSA-N 0.000 description 3
- GIQPXRWJJJJIQD-UHFFFAOYSA-N triphenyl-[[4-(sulfanylmethyl)phenyl]methyl]phosphanium;bromide Chemical compound [Br-].C1=CC(CS)=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 GIQPXRWJJJJIQD-UHFFFAOYSA-N 0.000 description 3
- VUGQMIVPQIAHJC-UHFFFAOYSA-N (4-methylphenyl)-diphenyl-(4-sulfanylbutyl)phosphanium;bromide Chemical compound [Br-].C1=CC(C)=CC=C1[P+](CCCCS)(C=1C=CC=CC=1)C1=CC=CC=C1 VUGQMIVPQIAHJC-UHFFFAOYSA-N 0.000 description 2
- RBZMSGOBSOCYHR-UHFFFAOYSA-N 1,4-bis(bromomethyl)benzene Chemical compound BrCC1=CC=C(CBr)C=C1 RBZMSGOBSOCYHR-UHFFFAOYSA-N 0.000 description 2
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- DKNVLJGPGQBWQD-UHFFFAOYSA-N SCCCC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=C(C=C1)CCS.[Br-] Chemical compound SCCCC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=C(C=C1)CCS.[Br-] DKNVLJGPGQBWQD-UHFFFAOYSA-N 0.000 description 2
- FCRDOCKVBUOKKL-UHFFFAOYSA-N SCCC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=C(C=C1)CCS.[Br-] Chemical compound SCCC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=C(C=C1)CCS.[Br-] FCRDOCKVBUOKKL-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- GPAYUJZHTULNBE-UHFFFAOYSA-O diphenylphosphanium Chemical compound C=1C=CC=CC=1[PH2+]C1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-O 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- HILSVOIVEJVFOZ-UHFFFAOYSA-N triphenyl(4-sulfanylbutyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCS)C1=CC=CC=C1 HILSVOIVEJVFOZ-UHFFFAOYSA-N 0.000 description 2
- SRXRDBJFXOVDOB-UHFFFAOYSA-N triphenyl(5-sulfanylpentyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCCS)C1=CC=CC=C1 SRXRDBJFXOVDOB-UHFFFAOYSA-N 0.000 description 2
- NPOUPLMXLITWJL-UHFFFAOYSA-N triphenyl(6-sulfanylhexyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCCCS)C1=CC=CC=C1 NPOUPLMXLITWJL-UHFFFAOYSA-N 0.000 description 2
- QJIMTLTYXBDJFC-UHFFFAOYSA-N (4-methylphenyl)-diphenylphosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QJIMTLTYXBDJFC-UHFFFAOYSA-N 0.000 description 1
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 1
- IBODDUNKEPPBKW-UHFFFAOYSA-N 1,5-dibromopentane Chemical compound BrCCCCCBr IBODDUNKEPPBKW-UHFFFAOYSA-N 0.000 description 1
- SGRHVVLXEBNBDV-UHFFFAOYSA-N 1,6-dibromohexane Chemical compound BrCCCCCCBr SGRHVVLXEBNBDV-UHFFFAOYSA-N 0.000 description 1
- ZQXIMYREBUZLPM-UHFFFAOYSA-N 1-aminoethanethiol Chemical compound CC(N)S ZQXIMYREBUZLPM-UHFFFAOYSA-N 0.000 description 1
- GNETVHIDZPYGGD-UHFFFAOYSA-N 1-aminoethanethiol;hydrochloride Chemical compound Cl.CC(N)S GNETVHIDZPYGGD-UHFFFAOYSA-N 0.000 description 1
- IYSVFZBXZVPIFA-UHFFFAOYSA-N 1-ethenyl-4-(4-ethenylphenyl)benzene Chemical group C1=CC(C=C)=CC=C1C1=CC=C(C=C)C=C1 IYSVFZBXZVPIFA-UHFFFAOYSA-N 0.000 description 1
- DXBJXKJWSYXGLZ-UHFFFAOYSA-N 1-pyridin-2-ylethanethiol Chemical compound CC(S)C1=CC=CC=N1 DXBJXKJWSYXGLZ-UHFFFAOYSA-N 0.000 description 1
- QWFMDSOYEQHWMF-UHFFFAOYSA-N 2,3-bis(ethenyl)benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(C=C)=C1C=C QWFMDSOYEQHWMF-UHFFFAOYSA-N 0.000 description 1
- MLCQXUZZAXKTSG-UHFFFAOYSA-N 2-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C=1C=CC=C(O)C=1C(C)(C)C1=CC=C(O)C=C1 MLCQXUZZAXKTSG-UHFFFAOYSA-N 0.000 description 1
- AXSMNPPSEOLAGB-UHFFFAOYSA-N 2-pyridin-4-ylethanethiol;hydrochloride Chemical compound Cl.SCCC1=CC=NC=C1 AXSMNPPSEOLAGB-UHFFFAOYSA-N 0.000 description 1
- WMVYYHAZJBKTRE-UHFFFAOYSA-N 3,3-diphenylpropyl-[[4-(sulfanylmethyl)phenyl]methyl]phosphanium;bromide Chemical compound [Br-].C1=CC(CS)=CC=C1C[PH2+]CCC(C=1C=CC=CC=1)C1=CC=CC=C1 WMVYYHAZJBKTRE-UHFFFAOYSA-N 0.000 description 1
- BJDNCJGRAMGIRU-UHFFFAOYSA-M 4-bromobutyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCBr)C1=CC=CC=C1 BJDNCJGRAMGIRU-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- KBMYOIWTYYRQOM-UHFFFAOYSA-N CS[N+](SC)(SC)CCC Chemical compound CS[N+](SC)(SC)CCC KBMYOIWTYYRQOM-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920000557 Nafion® Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- DIUGRRRGUZGXGW-UHFFFAOYSA-N [4-(3,3-diphenylpropylphosphanylmethyl)phenyl]methanethiol Chemical class C1=CC(CS)=CC=C1CPCCC(C=1C=CC=CC=1)C1=CC=CC=C1 DIUGRRRGUZGXGW-UHFFFAOYSA-N 0.000 description 1
- CJISBXYVUTVIDO-UHFFFAOYSA-N [Br-].SCC1=CC=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=C(C=C2)CCS)C=C1 Chemical compound [Br-].SCC1=CC=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=C(C=C2)CCS)C=C1 CJISBXYVUTVIDO-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010543 cumene process Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- AAXGWYDSLJUQLN-UHFFFAOYSA-N diphenyl(propyl)phosphane Chemical compound C=1C=CC=CC=1P(CCC)C1=CC=CC=C1 AAXGWYDSLJUQLN-UHFFFAOYSA-N 0.000 description 1
- CLEWFMVDUOZGPX-UHFFFAOYSA-O diphenyl-[4-(2-sulfanylethyl)phenyl]-(3-sulfanylpropyl)phosphanium Chemical group SCCC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=C(C=C1)CCS CLEWFMVDUOZGPX-UHFFFAOYSA-O 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- DUYAAUVXQSMXQP-UHFFFAOYSA-N ethanethioic S-acid Chemical class CC(S)=O DUYAAUVXQSMXQP-UHFFFAOYSA-N 0.000 description 1
- 238000000434 field desorption mass spectrometry Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
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- 238000007429 general method Methods 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
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- 229910052751 metal Inorganic materials 0.000 description 1
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- 230000004048 modification Effects 0.000 description 1
- 238000002715 modification method Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 238000000954 titration curve Methods 0.000 description 1
- OHAXMELREREYJC-UHFFFAOYSA-O triphenyl(3-sulfanylpropyl)phosphanium Chemical group C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCS)C1=CC=CC=C1 OHAXMELREREYJC-UHFFFAOYSA-O 0.000 description 1
- DQZWWKPTBWWDIH-UHFFFAOYSA-O triphenyl(4-sulfanylbutyl)phosphanium Chemical group C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCS)C1=CC=CC=C1 DQZWWKPTBWWDIH-UHFFFAOYSA-O 0.000 description 1
- SWKBYPFCMLXKMJ-UHFFFAOYSA-O triphenyl(5-sulfanylpentyl)phosphanium Chemical group C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCCS)C1=CC=CC=C1 SWKBYPFCMLXKMJ-UHFFFAOYSA-O 0.000 description 1
- FQDARNJQSZADEX-UHFFFAOYSA-O triphenyl(6-sulfanylhexyl)phosphanium Chemical group C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCCCS)C1=CC=CC=C1 FQDARNJQSZADEX-UHFFFAOYSA-O 0.000 description 1
- TVGUEVYAFAQINL-UHFFFAOYSA-O triphenyl-[[4-(sulfanylmethyl)phenyl]methyl]phosphanium Chemical group C1=CC(CS)=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 TVGUEVYAFAQINL-UHFFFAOYSA-O 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 210000004885 white matter Anatomy 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/08—Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/16—Organic material
- B01J39/18—Macromolecular compounds
- B01J39/20—Macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/40—Introducing phosphorus atoms or phosphorus-containing groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- B01J31/08—Ion-exchange resins
- B01J31/10—Ion-exchange resins sulfonated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/20—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms using aldehydes or ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/15—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with all hydroxy groups on non-condensed rings, e.g. phenylphenol
- C07C39/16—Bis-(hydroxyphenyl) alkanes; Tris-(hydroxyphenyl)alkanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5442—Aromatic phosphonium compounds (P-C aromatic linkage)
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2004-196828 | 2004-07-02 | ||
| JP2004196828 | 2004-07-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2007104029A RU2007104029A (ru) | 2008-08-10 |
| RU2337753C1 true RU2337753C1 (ru) | 2008-11-10 |
Family
ID=35782614
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2007104029A RU2337753C1 (ru) | 2004-07-02 | 2005-06-14 | Модифицированная ионообменная смола и способ получения бисфенолов |
Country Status (9)
| Country | Link |
|---|---|
| US (3) | US7968612B2 (ja) |
| EP (1) | EP1785188B1 (ja) |
| JP (1) | JP5126771B2 (ja) |
| KR (1) | KR100845507B1 (ja) |
| CN (1) | CN100546720C (ja) |
| ES (1) | ES2432042T3 (ja) |
| RU (1) | RU2337753C1 (ja) |
| TW (2) | TWI283191B (ja) |
| WO (1) | WO2006003803A1 (ja) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2708309C1 (ru) * | 2019-03-26 | 2019-12-05 | Федеральное государственное бюджетное учреждение науки Институт химии Дальневосточного отделения Российской академии наук (ИХ ДВО РАН) | Способ получения гидрофобного нефтесорбента и устройство для его осуществления |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008081898A1 (ja) * | 2006-12-28 | 2008-07-10 | Tohoku Techno Arch Co., Ltd. | 強塩基性陰イオン交換樹脂の再生方法 |
| JP5247184B2 (ja) * | 2008-02-21 | 2013-07-24 | 三井化学株式会社 | ビスフェノールａの製造方法 |
| US8436057B1 (en) * | 2010-02-17 | 2013-05-07 | U.S. Department Of Energy | Anion exchange membrane |
| WO2018200278A1 (en) * | 2017-04-24 | 2018-11-01 | Badger Licensing Llc | Catalyst system and process for producing bisphenol-a |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3992432A (en) * | 1967-04-05 | 1976-11-16 | Continental Oil Company | Phase transfer catalysis of heterogeneous reactions by quaternary salts |
| US3853951A (en) * | 1971-07-14 | 1974-12-10 | American Cyanamid Co | Preparation of 9-oxo-13-trans-prostenoic acid esters by alanate addition to cyclopentenone |
| US3836581A (en) * | 1971-12-16 | 1974-09-17 | American Cyanamid Co | 1-alkoximino-2-(omega-substituted-alkyl)-2-cyclopentenes |
| US4303551A (en) * | 1976-02-23 | 1981-12-01 | Varen Technology | Supported catalyst |
| US4423252A (en) * | 1980-08-07 | 1983-12-27 | Mitsubishi Chemical Industries Limited | Process for preparing bisphenols |
| JPS5735533A (en) | 1980-08-12 | 1982-02-26 | Mitsubishi Chem Ind Ltd | Preparation of bisphenol |
| JPS62178532A (ja) | 1986-01-30 | 1987-08-05 | Mitsui Toatsu Chem Inc | ビスフエノ−ルの製造法 |
| IL93020A (en) * | 1990-01-09 | 1995-06-29 | Yeda Res & Dev | Biosensors comprising a lipid bilayer doped with ion channels anchored to a recording electrode by bridging molecules |
| ATE155741T1 (de) * | 1990-04-27 | 1997-08-15 | Canon Kk | Aufzeichnungsverfahren und -gerät |
| US5233096A (en) * | 1990-11-16 | 1993-08-03 | Rohm And Haas Company | Acidic catalyst for condensation reactions |
| CA2054386A1 (en) | 1990-11-16 | 1992-05-17 | Eric Gustave Lundquist | Acidic catalyst for condensation reactions |
| JPH0597741A (ja) | 1991-10-11 | 1993-04-20 | Chiyoda Corp | ビスフエノール化合物の製造方法 |
| DE4312039A1 (de) * | 1993-04-13 | 1994-10-20 | Bayer Ag | Optimierte Ionenaustauscherschüttungen für die Bis-phenol-A Synthese |
| JP3656271B2 (ja) * | 1994-04-08 | 2005-06-08 | 三菱化学株式会社 | 変性イオン交換樹脂及びその使用 |
| US5589517A (en) * | 1994-04-08 | 1996-12-31 | Mitsubishi Chemical Corporation | Modified ion exchange resins and use thereof |
| US5463140A (en) * | 1994-08-31 | 1995-10-31 | The Dow Chemical Company | Process for making polyphenols from ketones or aldehydes and phenols |
| JPH0871433A (ja) * | 1994-09-02 | 1996-03-19 | Mitsubishi Chem Corp | イオン交換樹脂 |
| JPH0889819A (ja) | 1994-09-20 | 1996-04-09 | Mitsubishi Chem Corp | イオン交換樹脂 |
| JP3757517B2 (ja) * | 1997-01-29 | 2006-03-22 | 三菱化学株式会社 | イオン交換樹脂及びこれを用いるビスフェノールの製法 |
| JP3757516B2 (ja) * | 1997-01-29 | 2006-03-22 | 三菱化学株式会社 | イオン交換樹脂及びこれを用いるビスフェノールの製造方法 |
| JP3752780B2 (ja) * | 1997-05-20 | 2006-03-08 | 三菱化学株式会社 | イオン交換樹脂及びこれを用いるビスフェノールの製造方法 |
| JP3826489B2 (ja) * | 1997-05-29 | 2006-09-27 | 三菱化学株式会社 | イオン交換樹脂およびその使用 |
| WO1999006145A1 (en) * | 1997-07-29 | 1999-02-11 | E.I. Du Pont De Nemours And Company | Process for the preparation of a catalytic microcomposite from a silicate and a highly fluorinated ion exchange resin |
| JP3858384B2 (ja) * | 1997-10-21 | 2006-12-13 | 三菱化学株式会社 | イオン交換樹脂及びこれを用いるビスフェノール類の製造方法 |
| JP3700361B2 (ja) * | 1997-12-18 | 2005-09-28 | 三菱化学株式会社 | イオン交換樹脂及びこれを触媒とするビスフェノール類の製造方法 |
| NO305825B1 (no) | 1998-06-19 | 1999-08-02 | Egil Jensen | Skrellemaskin |
| JP4256998B2 (ja) * | 1999-10-27 | 2009-04-22 | 株式会社トクヤマ | シラン化合物の不均化反応生成物の製造方法 |
| US20050014910A1 (en) * | 2000-02-16 | 2005-01-20 | Lepilleur Carole A. | Toughened vinyl ester resins |
| JP2001335522A (ja) * | 2000-05-25 | 2001-12-04 | Mitsubishi Chemicals Corp | ビスフェノールの製造方法 |
| ATE424925T1 (de) * | 2000-09-19 | 2009-03-15 | Dow Global Technologies Inc | Verfahren zur herstellung eines starksauren kationenaustauscherharzes |
| US6414200B1 (en) * | 2000-12-19 | 2002-07-02 | General Electric Company | Silylmethanethiols as promoters for bisphenol production |
| US6486364B2 (en) * | 2000-12-19 | 2002-11-26 | General Electric Company | Amine modified catalysts for bisphenol production |
| US6730816B2 (en) * | 2000-12-29 | 2004-05-04 | Rohm And Haas Company | High productivity bisphenol-A catalyst |
| JP4658355B2 (ja) * | 2001-03-05 | 2011-03-23 | 出光興産株式会社 | ビスフェノールａの製造方法 |
| US6534686B1 (en) * | 2001-09-18 | 2003-03-18 | General Electric Company | Method for producing bisphenol catalysts and bisphenols |
| US6620939B2 (en) * | 2001-09-18 | 2003-09-16 | General Electric Company | Method for producing bisphenol catalysts and bisphenols |
| JP4050053B2 (ja) * | 2001-12-27 | 2008-02-20 | 出光興産株式会社 | ビスフェノール類製造用触媒及び該触媒を用いるビスフェノール類の製造方法 |
| JP4595349B2 (ja) * | 2004-02-26 | 2010-12-08 | 三菱化学株式会社 | 変性イオン交換体の製造方法 |
| US20070073091A1 (en) * | 2003-09-10 | 2007-03-29 | Takashi Terajima | Process for producing bisphenol a |
| JP4147202B2 (ja) * | 2003-09-30 | 2008-09-10 | 三井化学株式会社 | 改質酸性イオン交換樹脂触媒およびそれを用いたビスフェノール類の製造方法 |
| JP2006340563A (ja) | 2005-06-06 | 2006-12-14 | Matsushita Electric Ind Co Ltd | Ｄｃ−ｄｃコンバータ |
-
2005
- 2005-06-14 CN CNB2005800224069A patent/CN100546720C/zh not_active Expired - Fee Related
- 2005-06-14 ES ES05751534T patent/ES2432042T3/es active Active
- 2005-06-14 US US11/631,292 patent/US7968612B2/en active Active
- 2005-06-14 EP EP05751534.8A patent/EP1785188B1/en active Active
- 2005-06-14 RU RU2007104029A patent/RU2337753C1/ru active
- 2005-06-14 KR KR1020067026817A patent/KR100845507B1/ko active IP Right Grant
- 2005-06-14 JP JP2006519607A patent/JP5126771B2/ja active Active
- 2005-06-14 WO PCT/JP2005/011206 patent/WO2006003803A1/ja active Application Filing
- 2005-06-27 TW TW94121386A patent/TWI283191B/zh not_active IP Right Cessation
- 2005-06-27 TW TW96107493A patent/TWI320042B/zh active
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2011
- 2011-05-19 US US13/111,600 patent/US20110224461A1/en not_active Abandoned
- 2011-05-19 US US13/111,573 patent/US8426479B2/en active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2708309C1 (ru) * | 2019-03-26 | 2019-12-05 | Федеральное государственное бюджетное учреждение науки Институт химии Дальневосточного отделения Российской академии наук (ИХ ДВО РАН) | Способ получения гидрофобного нефтесорбента и устройство для его осуществления |
Also Published As
| Publication number | Publication date |
|---|---|
| TWI283191B (en) | 2007-07-01 |
| TW200734347A (en) | 2007-09-16 |
| US20110224461A1 (en) | 2011-09-15 |
| KR100845507B1 (ko) | 2008-07-10 |
| US20110224315A1 (en) | 2011-09-15 |
| ES2432042T3 (es) | 2013-11-29 |
| TW200611749A (en) | 2006-04-16 |
| EP1785188A1 (en) | 2007-05-16 |
| CN100546720C (zh) | 2009-10-07 |
| EP1785188A4 (en) | 2012-02-29 |
| WO2006003803A1 (ja) | 2006-01-12 |
| JPWO2006003803A1 (ja) | 2008-04-17 |
| EP1785188B1 (en) | 2013-08-07 |
| US20080051480A1 (en) | 2008-02-28 |
| KR20070028434A (ko) | 2007-03-12 |
| TWI320042B (en) | 2010-02-01 |
| JP5126771B2 (ja) | 2013-01-23 |
| RU2007104029A (ru) | 2008-08-10 |
| US7968612B2 (en) | 2011-06-28 |
| US8426479B2 (en) | 2013-04-23 |
| CN1980737A (zh) | 2007-06-13 |
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